高等学校化学学报 ›› 2014, Vol. 35 ›› Issue (2): 314-318.doi: 10.7503/cjcu20130613

• 有机化学 • 上一篇    下一篇

双酚A葡萄糖醛酸苷的高效制备

杨刚1, 朱亮亮2, 吕侠2, 吴大畅1, 夏杨柳2, 马骁驰1, 辛毅1, 侯洁1()   

  1. 1. 大连医科大学生物技术系, 大连116044
    2. 中国科学院大连化学物理研究所, 大连116023
  • 收稿日期:2013-07-04 出版日期:2014-02-10 发布日期:2014-01-02
  • 作者简介:联系人简介: 侯 洁, 女, 博士, 讲师, 主要从事靶向抗肿瘤药物研究及药物代谢研究. E-mail:houjie@nankai.edu.cn
  • 基金资助:
    国家自然科学基金(批准号: 81001473, 81273590, 81302793)、 国家“九七三”计划项目(批准号: 2013CB531800)、 辽宁省教育厅科研项目(批准号: L2013345)和辽宁省科技厅自然科学基金(批准号: 2013023049)资助

Highly Efficient Preparation of Bisphenol A Glucuronide

YANG Gang1, ZHU Liangliang2, LÜ Xia2, WU Dachang1, XIA Yangliu2, MA Xiaochi1, XIN Yi1, HOU Jie1,*()   

  1. 1. Department of Biotechnology, Dalian Medical University, Dalian 116044, China
    2. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
  • Received:2013-07-04 Online:2014-02-10 Published:2014-01-02
  • Contact: HOU Jie E-mail:houjie@nankai.edu.cn
  • Supported by:
    † Supported by the National Natural Science Foundation of China(Nos.81001473, 81273590, 81302793), National Basic Research Program of China(No.2013CB531800), Science Project of Liaoning Provincial Department of Education, China(No.L2013345) and Natural Science Foundation of Liaoning Province, China(No.2013023049)

摘要:

采用鼠肝微粒体(RLM)生物转化法, 利用正交实验在体外实现了双酚A(BPA)向双酚A葡萄糖醛酸苷(BPA-G)的高效转化, 同时借助新型色谱分离材料C18WAX及固相萃取技术实现了BPA-G的高效富集与纯化, 并对产物进行了结构表征.

关键词: 双酚A, 鼠肝微粒体, 双酚A葡萄糖醛酸苷, 固相萃取

Abstract:

Bisphenol A(BPA), an industrial chemical, has been present in many hard plastic bottles, metal-based food and beverage cans. Many governments are trying to reduce the human exposure to BPA because it is really a readily accessible toxin for human. BPA can be extensively metabolized to bisphenol A-β-O-glucuronide(BPA-G) by UDP-glucuronosyltransferases(UGTs), thus the biological activities of BPA-G should be studied intensively. However, the studies on BPA-G are very limited due to the difficulty for preparation of BPA-G. In this work, the BPA-G was prepared using BPA as the starting material and rat liver microsomes(RLM) as the enzyme source. A series of orthogonal experiments was designed and performed to determine the optimal reaction conditions for BPA glucuronidation in RLM. After incubation under the optimal reaction conditions, the conversion of BPA was higher than 98%. A unique solid-phase extraction column(SPE) packed with C18WAX was used to enrich and purify the product BPA-G with high yield. Finally, the product was identified by both ESI-MS and NMR techniques.

Key words: Bisphenol A, Rat liver microsome, Bisphenol A-β-O-glucuronide, Solid-phase extraction